The Lawyer Who Loves Getting Ready for Dates

Illustration: Marylu E. Herrera

This week, a woman tries new things in bed and enjoys her post-divorce dating life: 45, single, New York.

DAY ONE

6:14 a.m. I don’t know how you’re supposed to feel the morning after you get your ass eaten for the first time. My life is not unlike Toby Fleishman’s from Fleishman Is in Trouble. I’m freshly single and discovering things at age 45. Last night, what I learned was that ass play is a whole new level of pleasure I will never scoff at again.

8 a.m. I don’t have my kids this weekend, so I try to lie in bed and do nothing, a luxury I dreamed about for the last ten years while married and raising little ones. I try not to take this “lying around and doing nothing” for granted, though I do miss my kids.

9 a.m. Coffee and check texts and emails. I’m a lawyer with my own practice, and today I’m giving myself a day off.

1 p.m. My date last night was with a guy I’ll call Ted, whom I met online and have seen a couple times. Ted isn’t particularly cute or tall or successful, but he’s a flirt and confident as shit as well as sexually insatiable. I like Ted. I don’t think I can fall in love with him, but I’m having fun seeing him. It’s definitely not exclusive or anything even close. We fucked on our first date, but last night was the first time I let him explore me everywhere. And I loved it.

4 p.m. I’m doing some early holiday shopping in the city, drinking a coffee, and happy to be alive.

6 p.m. FaceTime with my kids to check in. I am happy (but also sad) to see my ex-husband’s face. I miss him sometimes, but I have to remind myself about how miserable we were. We fought all the time, for years, relentlessly, about anything and everything. It was sheer emotional torture for both of us. About a year ago, we both agreed divorce was best for the kids. We tried to handle everything as amicably as possible, and honestly it wasn’t all that painful. I’m proud of us. And my kids are doing as well as can be expected.

9 p.m. Ted texts to see if I’m watching the same show he’s watching, The White Lotus. (We are going to watch Fleishman together … I only read the book!) We proceed to watch and text our thoughts simultaneously. Ted is very fun, and he brings a certain lightness to my day. It’s that simple.

DAY TWO

9 a.m. Monday morning, so I’m showered, dressed, and heading out the door.

10 a.m. My work entails a lot of corporate bullshit and grinding. I can’t pretend it’s glamorous, but I’m good at what I do and the money is great. I am the daughter of immigrants who came here with nothing, and I never take my career or financial stability for granted.

1 p.m. Break for lunch at my desk (vegan Caesar salad even though I’m not vegan) and swiping on the apps. It’s true that most people on Bumble and Hinge are creepy or fake or totally vile for one reason or another, but if you look hard enough, there are some potentials. I’ve been talking to a guy named Boris who I’m supposed to see tonight for drinks. Can I fuck a man named Boris? TBD.

6 p.m. Wrap things up at work. Check in with my kids, who I’m picking up tomorrow morning, and head home.

7 p.m. I take a shower and eat some olives and almonds. I’m very hungry, but I don’t want to eat a huge meal before the date. Brush my teeth and head to the hotel bar uptown where we’re meeting.

8 p.m. Boris is strikingly handsome! He undersold himself. He’s an international-businessman type and very confident and masculine. We have martinis at the bar.

9 p.m. Boris is on his third martini.

10 p.m. Feeling a little turned off by his drinking and getting a weird vibe. I’m about ready to call it and go home when Boris puts his hand on my thigh and asks if I want to get a room. I know the rooms at this hotel are about $1,000 or more, so it doesn’t feel as “cheap” as it sounds, but it does seem a bit dangerous. Is Boris a murderer? I don’t think so. But I’m not horny for him, honestly. I politely decline and he takes it well, which makes me think that maybe I actually should have gone upstairs with him. Oh well.

DAY THREE

8 a.m. I pick up my kids. My ex lives nearby, and we have a pretty good system. I’ve missed them, and it’s wonderful to have them in my arms.

8:15 a.m. I hastily shepherd everyone off to school and get myself to work.

11 a.m. I don’t think I’ll hear from Boris again. He just wants to fuck someone. Which is fine, but I’d rather do that with Ted. What I’m really looking for is someone to light my fire. I want to have a crush, or even an aching love. It’s been a long time. But I’m happy to have safe, casual sex for now. Why be boring?

1 p.m. A few weeks ago, I met a guy named Niles who was British and hot as hell and a really good time. Dinner in Soho, drinks at the Bowery Hotel, and the hottest make-out session on the street. It was so much fun, and I was dying to sleep with him. We decided to continue the fun another night because we both had epic workdays the next day, and then I never heard from him again. I’m pretty good at reading the room, and I could have sworn he liked me. It was really weird. But anyway, he just texted me. “I’m back in town, what are you up to?” Hmmm. I never knew he left town.

4 p.m. Ted is trying to hang tonight, but I’ve been flirting hard-core with Niles all day and I’m going to try to him tonight instead. Poor Ted. He ate my ass and now is getting nothing in return.

7 p.m. I’m home, getting the kids ready for bed, waiting to hear from Niles about where to meet up later. I have a babysitter on hold. Is Niles ghosting?

8 p.m. He is fucking ghosting me.

9 p.m. I cancel the babysitter and take out my vibrator. Sometimes my orgasms are so strong that my throat burns afterward from screaming or swallowing a scream, and sometimes they feel almost, like, desensitized. Like there’s a dead wire in there. I guess it’s a product of my age. I try not to worry about any of that stuff too much.

10 p.m. Niles sucks. I’m going to bed.

DAY FOUR

8 a.m. The usual morning grind.

10 a.m. I’m horny today. Maybe I’ll see Ted tonight. He is really good in bed. I just wish I respected him more or ached for him more.

1 p.m. Swiping online. I try to avoid the polyamory people. It’s just not my scene, even though I should be more open minded, probably. I match with someone named Rory who, from our brief exchange, sounds like a male version of me. Our jobs are almost identical; we even know some of the same people. Rory is cute and seems fun. It’s always like, What’s his secret damage? Like, How is this person terrible? I guess they’re wondering the same about me.

5 p.m. Ted and I make plans to grab dinner and wine. He chooses excellent wine. He also never lets me pay, which I’m fine with, but I don’t know how he affords such fancy wine. He’s a social worker.

8 p.m. Babysitter arrives.

9 p.m. With Ted. We’re laughing and drinking. He asks a lot about my kids. He doesn’t have kids, and he’s sad about that. I feel protective, though, because he won’t be sharing my kids with me. I know that. So there’s an awkward undertone there. I try to drink more to forget about that.

9:45 p.m. We’re at his place and our clothes are off. He goes down on me, front and back, for a long time, and then we start to fuck. It’s so pleasurable. I do have to kind of pretend that I’m with someone else, not Ted, but physically it’s extremely blissful.

11 p.m. Home at my place, happy with the sex, ready to sleep.

DAY FIVE

9 a.m. I don’t know. I feel a bit depressed today. It’s from all the drinking, and I think the Ted thing has to end. He likes me. I feel like I’m being unfair to him, and that’s weighing on my psyche.

1 p.m. I text with Rory. He’s not officially divorced yet, which I have no problem with. As a lawyer, I know how long everything takes.  We plan to meet up tomorrow since I really need a night to purify and sleep.

3 p.m. I get my highlights done at the place I’ve gone to forever and ask them to wash my hair for an extra ten minutes for an extra big tip. I just need some comfort today.

5 p.m. The kids and I go out for sushi. I love hearing about their lives and not thinking about mine.

9 p.m. Early bedtime for me!

DAY SIX 

7:15 a.m. I wake up to a text from Ted that he wrote last night. He is ending things with me! What a strange turn of events. He said he knows I’m not really feeling it and neither is he, so we should just be friends. Ted’s a good man. I’ll text him later when I’m more awake.

1 p.m. I have a shit-ton of work today. All I do is keep my head down.

4 p.m. Still working.

6 p.m. Still working.

7:30 p.m. By the time I’m home with my kids, I’m just a zombie. Rory wants to meet up, but I push it until tomorrow night. He has kids and understands that plans change, and I respect his flexibility.

8 p.m. I watch Fleishman without Ted because I don’t think that’s ever going to happen … and I really like it. I personally don’t think Jesse Eisenberg’s character could get that much pussy, but I could be wrong. Women sure love doctors.

DAY SEVEN

9 a.m. I drop my kids at their father’s house and come home to clean my trashed apartment. With the right coffee and the right podcast, this is not as bad as it could be.

11:30 a.m. I get a pedicure with no nail polish, just because I want my feet rubbed and touched. I love any kind of massage. It’s all I want out of life, honestly: massages.

1:30 p.m. Rory suggests a new restaurant where he can get us a reservation. I tell him I’m in. Dinner is a dangerous prospect when you don’t know a guy — it could be the longest, worst dinner of my life. But I really want to try this food, and Rory seems great, so fuck it!

5 p.m. I love getting ready for a date. A glass of wine. Some music. Putting on lingerie and trying on clothes. Again, it’s one of those things you don’t treasure until you’ve been in the throes of unglamorous motherhood for so long.

7 p.m. Okay, so, Rory is cute, but short, but cute! I’m pretty short, so it’s not a big deal. He has nice “manly” hands, a beautiful smile, and he’s dressed really well and I could be into him.

7:45 p.m. We’ve ordered food and wine. The conversation is flowing. Is he boring? He talks a lot about work. He might be boring? Or maybe it’s just great to connect with someone who understands your work life on the level I do, and he’s leaning in to that. Anyway, I do find him sexy.

9 a.m. The meal was great, and now it’s like … what next? He suggests a drink at his place (code for “going home to fuck”), but I decide to pump the breaks. I could end up liking Rory and would rather have a slow burn.

9:15 p.m. We kiss outside the restaurant, awaiting our Ubers. Classic first-date scene. His mouth tastes great and the kiss is incredibly arousing. I want to put my hands under his pants and rub his cock, but I don’t. Then the Ubers arrives and we say, “See you soon.”

Want to submit a sex diary? Email [email protected] and tell us a little about yourself (and read our submission terms here.)